US2367469A - Polyamides - Google Patents
Polyamides Download PDFInfo
- Publication number
- US2367469A US2367469A US383226A US38322641A US2367469A US 2367469 A US2367469 A US 2367469A US 383226 A US383226 A US 383226A US 38322641 A US38322641 A US 38322641A US 2367469 A US2367469 A US 2367469A
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- US
- United States
- Prior art keywords
- water
- acid
- polyamides
- acids
- soluble
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and polycarboxylic acids
Definitions
- the new hydrophilic polyamides described herein can be produced by condensing w-l'ilOl'lO- and for many purposes as, for instance, for gelatin substitutes binding agents, sizing and finishing aminomonocarboxylic acids having at least four agents, and thickening agents for printing pastes.
- the polyamide-forming compositions in which the reactants are diamines and dicarboxylic acids having long chains, likewise yield hydrophilic, water-soluble condensation products in the presence of inorganic acids.
- reactants with a long carbon chain we mention mixtures of diamines or derivatives thereof having at least five carbon atoms between the amino groups and dicarboxylic acids or derivatives thereof (if desired substituted by aliphatic or cyclic radicals) having at least four carbon atoms between the carboxyl groups.
- the halogen hydracids are preferably employed.
- the process of the invention may also be accomplished with other strong fmonobasic mineral acids as, for instance, nitric acid or with polybasic inorganic acids.
- the condensation orpolymerization is con-- veniently carried out, by heating at 200-250 C. in the absence of air. It is not necessary to use a special catalyst since the'mineral acid already effects a suflicient acceleration of the condensation procedure.
- the acid is preferably added in the form or the salt of the diamine to be con densedor a derivative thereof.
- interpolyamides in which case the choice of the reactants depends onthe intended use and may be made regardless of. the desired sensitivity to water since this factOr is solely controlled by the mineral acid used.
- the new polyamides are used in various-forms
- Example I 80 g. of hexamethylenediamine adipate and 20 cc. of concentrated hydrochloric acid (37.8%) are intimately mixed and heated together in an atmosphere of carbon dioxide at 21l-222 C. during 20 hours after the air is carefully removed by carbon dioxide. yellowish brown and soluble in water and methanol.
- Example II 75 g. of hexamethylenediamine adipate and 23 g. of e-aminocaproic-acid-hydrochlorideare intimately mixed and condensed in thesame way as describedin Example I.
- the thus resulting product is yellowish brown and soluble in water and hot alcohols.
- Example III g. of hexamethylenediamine adipate, 40 g.
- Example II e-caprolactam and 50 g. of e-aminocaproicacid-hydrochloride are polymerized in the mannet as described in Example I.
- the polymer thus prepared is a tenaciou transparent yellow product soluble in water and aqueous alcohols.
- Example IV A mixture of 60.6 g. of sebacic acid, 259 g. of
Description
Patented Jan. 16, 1945 2...: STATES PATENT orrlce POLYAIVWES Paul Miiller, Dessau, and Hans-Joachim Nicolai,
Dessau-Haideburg, Germany;
vested in the Alien Property Custodian No Drawing. Application March 13, 1941, serial No. 383,226. lln Germany March 14, 1940 1 Claim. (Cl. 260-78) Our present invention relates to polyamides, and in particular to a new method for preparing hydrophilic superpolyamides.
The new hydrophilic polyamides described herein can be produced by condensing w-l'ilOl'lO- and for many purposes as, for instance, for gelatin substitutes binding agents, sizing and finishing aminomonocarboxylic acids having at least four agents, and thickening agents for printing pastes.
The more detailed practice of the invention is illustrated by the following examples. There'are, of course, many forms of the invention other than these specific embodiments:
warm aqueous solution into the gel-state on cool- Under similar conditions the polyamide-forming compositions in which the reactants are diamines and dicarboxylic acids having long chains, likewise yield hydrophilic, water-soluble condensation products in the presence of inorganic acids.
It will be understood that mention herein of these polyamide-forming reactants, as in the case of the amino acids referred to above, is intended to include their equivalent amide-forming derivatives.
While polymers stable on boiling and insoluble in water and in usual solvents are obtained by the condensation of the diamines and dicarboxylic acids having long carbon chains, a content of more than 0.1 mol of inorganicacid anion in the polymer effects that the condensation products are capable of strongly swelling in water, alcohols or other hydrophilic solvents or dissolving therein. As reactants with a long carbon chain we mention mixtures of diamines or derivatives thereof having at least five carbon atoms between the amino groups and dicarboxylic acids or derivatives thereof (if desired substituted by aliphatic or cyclic radicals) having at least four carbon atoms between the carboxyl groups.
As inorganic acids the halogen hydracids are preferably employed. The process of the invention may also be accomplished with other strong fmonobasic mineral acids as, for instance, nitric acid or with polybasic inorganic acids.
The condensation orpolymerization is con-- veniently carried out, by heating at 200-250 C. in the absence of air. It is not necessary to use a special catalyst since the'mineral acid already effects a suflicient acceleration of the condensation procedure. The acid is preferably added in the form or the salt of the diamine to be con densedor a derivative thereof.
It is also possible to prepare interpolyamides in which case the choice of the reactants depends onthe intended use and may be made regardless of. the desired sensitivity to water since this factOr is solely controlled by the mineral acid used.
The new polyamides are used in various-forms Example I 80 g. of hexamethylenediamine adipate and 20 cc. of concentrated hydrochloric acid (37.8%) are intimately mixed and heated together in an atmosphere of carbon dioxide at 21l-222 C. during 20 hours after the air is carefully removed by carbon dioxide. yellowish brown and soluble in water and methanol.
If the amount of hydrochloric acid is decreased, water-insoluble polymers are obtained.
Example II 75 g. of hexamethylenediamine adipate and 23 g. of e-aminocaproic-acid-hydrochlorideare intimately mixed and condensed in thesame way as describedin Example I. The thus resulting product is yellowish brown and soluble in water and hot alcohols.
If the amount of e-aminocaproic-acid-hydrochloride is decreased, products are formed which have a small solubility'in water.
Example III g. of hexamethylenediamine adipate, 40 g.
of e-caprolactam and 50 g. of e-aminocaproicacid-hydrochloride are polymerized in the mannet as described in Example I. The polymer thus prepared is a tenaciou transparent yellow product soluble in water and aqueous alcohols.
If the amount of e-aminocaproic-acid-hydro-. chloride is lowered to 6.5 g., a milky water-insoluble polymer is produced.
Example IV A mixture of 60.6 g. of sebacic acid, 259 g. of
'The process of preparing water-soluble poly-' amides which comprises condensing approximately parts by weight of hexamethylenediamine adipate with about 23 parts or e-aminocaproic-acid-hydrochloride at from 211-222 C.
for twenty hours-with exclusion of air.
PAUL MOLLER. HANS-JOACHIM .NICOLAI.
The product thus obtained is
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2367469X | 1940-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2367469A true US2367469A (en) | 1945-01-16 |
Family
ID=7995535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US383226A Expired - Lifetime US2367469A (en) | 1940-03-14 | 1941-03-13 | Polyamides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2367469A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3407179A (en) * | 1965-05-12 | 1968-10-22 | Du Pont | Batch polymerization of aqueous diamine-dicarboxylic acid salt |
-
1941
- 1941-03-13 US US383226A patent/US2367469A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3407179A (en) * | 1965-05-12 | 1968-10-22 | Du Pont | Batch polymerization of aqueous diamine-dicarboxylic acid salt |
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